AU671284B2 - Method for delignifying and bleaching a lignocellulose material - Google Patents
Method for delignifying and bleaching a lignocellulose material Download PDFInfo
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- AU671284B2 AU671284B2 AU43333/93A AU4333393A AU671284B2 AU 671284 B2 AU671284 B2 AU 671284B2 AU 43333/93 A AU43333/93 A AU 43333/93A AU 4333393 A AU4333393 A AU 4333393A AU 671284 B2 AU671284 B2 AU 671284B2
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- pulp
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- 238000000034 method Methods 0.000 title claims abstract description 32
- 239000000463 material Substances 0.000 title claims abstract description 31
- 238000004061 bleaching Methods 0.000 title claims abstract description 24
- 239000011572 manganese Substances 0.000 claims abstract description 39
- 239000007800 oxidant agent Substances 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000003446 ligand Substances 0.000 claims abstract description 22
- -1 organometallic cation Chemical class 0.000 claims abstract description 22
- 150000001768 cations Chemical class 0.000 claims abstract description 15
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 230000001590 oxidative effect Effects 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 41
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 39
- 230000003647 oxidation Effects 0.000 claims description 36
- 230000008569 process Effects 0.000 claims description 25
- 229920001131 Pulp (paper) Polymers 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229920005610 lignin Polymers 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- 239000002023 wood Substances 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 5
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000012634 fragment Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- YUHVVTLNLCJEOB-UHFFFAOYSA-N [Cl].O=Cl=O Chemical compound [Cl].O=Cl=O YUHVVTLNLCJEOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 235000020299 breve Nutrition 0.000 claims 1
- MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002609 medium Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 10
- 229920002678 cellulose Polymers 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 9
- 239000012736 aqueous medium Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- RJTZQPTVNWCDBI-UHFFFAOYSA-N n,n'-bis(pyridin-2-ylmethyl)ethane-1,2-diamine Chemical compound C=1C=CC=NC=1CNCCNCC1=CC=CC=N1 RJTZQPTVNWCDBI-UHFFFAOYSA-N 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000004032 porphyrins Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- OEGPRYNGFWGMMV-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC OEGPRYNGFWGMMV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 230000033116 oxidation-reduction process Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000011121 hardwood Substances 0.000 description 3
- BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 description 3
- 229940025294 hemin Drugs 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- KXZQYLBVMZGIKC-UHFFFAOYSA-N 1-pyridin-2-yl-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CNCC1=CC=CC=N1 KXZQYLBVMZGIKC-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical class ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 2
- JCLFHZLOKITRCE-UHFFFAOYSA-N 4-pentoxyphenol Chemical compound CCCCCOC1=CC=C(O)C=C1 JCLFHZLOKITRCE-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019093 NaOCl Inorganic materials 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- JQRLYSGCPHSLJI-UHFFFAOYSA-N [Fe].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Fe].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JQRLYSGCPHSLJI-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000003592 biomimetic effect Effects 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- OSVXSBDYLRYLIG-UHFFFAOYSA-N dioxidochlorine(.) Chemical compound O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000002655 kraft paper Substances 0.000 description 2
- 150000002696 manganese Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FFIMOEOESOMAGV-UHFFFAOYSA-N n-[(6-methylpyridin-2-yl)methyl]-2-pyridin-2-yl-n-(pyridin-2-ylmethyl)ethanamine Chemical compound CC1=CC=CC(CN(CCC=2N=CC=CC=2)CC=2N=CC=CC=2)=N1 FFIMOEOESOMAGV-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
- VGUWFGWZSVLROP-UHFFFAOYSA-N 1-pyridin-2-yl-n,n-bis(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CN(CC=1N=CC=CC=1)CC1=CC=CC=N1 VGUWFGWZSVLROP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 239000004155 Chlorine dioxide Substances 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 241001484259 Lacuna Species 0.000 description 1
- 108010059896 Manganese peroxidase Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 241000222385 Phanerochaete Species 0.000 description 1
- 241000222393 Phanerochaete chrysosporium Species 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920002522 Wood fibre Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000019398 chlorine dioxide Nutrition 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- GOYYUYNOGNSLTE-UHFFFAOYSA-N copper;2-azanidylethylazanide Chemical compound [Cu+2].[NH-]CC[NH-].[NH-]CC[NH-] GOYYUYNOGNSLTE-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940013191 edex Drugs 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000003295 industrial effluent Substances 0.000 description 1
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 1
- 108010062085 ligninase Proteins 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- MHERDSVHKRZMJL-UHFFFAOYSA-N n-[(6-methylpyridin-2-yl)methyl]-1-pyridin-2-yl-n-(pyridin-2-ylmethyl)methanamine Chemical compound CC1=CC=CC(CN(CC=2N=CC=CC=2)CC=2N=CC=CC=2)=N1 MHERDSVHKRZMJL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
- 229940075931 sodium dithionate Drugs 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000010875 treated wood Substances 0.000 description 1
- 238000004832 voltammetry Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
- D21C9/10—Bleaching ; Apparatus therefor
- D21C9/1078—Bleaching ; Apparatus therefor with Mn-containing compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
- D21C9/10—Bleaching ; Apparatus therefor
- D21C9/1026—Other features in bleaching processes
- D21C9/1036—Use of compounds accelerating or improving the efficiency of the processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
- B01J2531/72—Manganese
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paper (AREA)
- Detergent Compositions (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9207577 | 1992-06-22 | ||
| FR9207577A FR2692499B1 (fr) | 1992-06-22 | 1992-06-22 | Procédé de délignification et de blanchiment d'une matière lignocellulosique. |
| PCT/FR1993/000613 WO1994000234A1 (fr) | 1992-06-22 | 1993-06-21 | Procede de delignification et de blanchiment d'une matiere lignocellulosique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4333393A AU4333393A (en) | 1994-01-24 |
| AU671284B2 true AU671284B2 (en) | 1996-08-22 |
Family
ID=9431007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU43333/93A Ceased AU671284B2 (en) | 1992-06-22 | 1993-06-21 | Method for delignifying and bleaching a lignocellulose material |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5630906A (de) |
| EP (1) | EP0647158B1 (de) |
| JP (1) | JPH08500856A (de) |
| AT (1) | ATE157024T1 (de) |
| AU (1) | AU671284B2 (de) |
| BR (1) | BR9306591A (de) |
| CA (1) | CA2138797A1 (de) |
| DE (1) | DE69313284D1 (de) |
| FI (1) | FI945990A (de) |
| FR (1) | FR2692499B1 (de) |
| NZ (1) | NZ253184A (de) |
| WO (1) | WO1994000234A1 (de) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2741340B1 (fr) * | 1995-11-16 | 1997-12-26 | Elf Aquitaine | Procede d'oxydation de substrats organiques en presence de complexes metalliques de ligands tetra-, penta- et hexacoordinants et catalyseurs d'oxydation les contenant |
| DE19614587A1 (de) * | 1996-04-13 | 1997-10-16 | Jaschinski Thomas Dipl Holzw | Verfahren und Bleichlösung zum Bleichen von cellulosischen Faserstoffen |
| DE19620241A1 (de) * | 1996-05-20 | 1997-11-27 | Patt R Prof Dr | Verfahren zum Delignifizieren von Zellstoffen und Verwendung eines Katalysators |
| CA2257891A1 (en) * | 1996-06-19 | 1997-12-24 | Roelant Mathijs Hermant | Bleach activation by an iron catalyst comprising a polydentate ligand containing at least six heteroatoms |
| CA2248476A1 (en) * | 1997-10-01 | 1999-04-01 | Unilever Plc | Bleach activation |
| DE69817832T2 (de) * | 1998-11-10 | 2004-10-07 | Unilever Nv | Bleich- und Oxidationskatalysator |
| DE69825166T2 (de) * | 1998-11-10 | 2004-11-25 | Unilever N.V. | Wasch- und Bleichzusammensetzungen |
| KR100555040B1 (ko) * | 1998-12-29 | 2006-05-16 | 주식회사 엘지생활건강 | 트리스(2-피리딜메틸)아민 망간 착화합물과 이를 함유한 표백제및 표백세제 조성물 |
| EP1101860A1 (de) * | 1999-11-19 | 2001-05-23 | Praxair Technology, Inc. | Verfahren zum Bleichen von Pulpe mittels aktivem Ozon |
| FR2813896A1 (fr) * | 2000-09-14 | 2002-03-15 | Atofina | Procede de delignification et blanchiment par un oxydant et un catalyseur d'oxydoreduction |
| US20100159521A1 (en) * | 2008-12-19 | 2010-06-24 | E. I. Du Pont De Nemours And Company | Ozone treatment of biomass to enhance enzymatic saccharification |
| US20100159515A1 (en) * | 2008-12-19 | 2010-06-24 | E.I. Du Pont De Nemours And Company | Oxidative pretreatment of biomass to enhance enzymatic saccharification |
| US20100159522A1 (en) * | 2008-12-19 | 2010-06-24 | E.I. De Pont De Nemours And Company | Organosolv and ozone treatment of biomass to enhance enzymatic saccharification |
| US8216809B2 (en) * | 2008-12-19 | 2012-07-10 | E I Du Pont De Nemours And Company | Organic solvent pretreatment of biomass to enhance enzymatic saccharification |
| US9511167B2 (en) | 2009-05-28 | 2016-12-06 | Gp Cellulose Gmbh | Modified cellulose from chemical kraft fiber and methods of making and using the same |
| US9512563B2 (en) | 2009-05-28 | 2016-12-06 | Gp Cellulose Gmbh | Surface treated modified cellulose from chemical kraft fiber and methods of making and using same |
| BRPI1012052A2 (pt) | 2009-05-28 | 2017-12-26 | Gp Cellulose Gmbh | fibras kraft hidrolisadas e quimicamente modificadas e métodos de produção e de branqueamento de fibras kraft |
| US9512237B2 (en) | 2009-05-28 | 2016-12-06 | Gp Cellulose Gmbh | Method for inhibiting the growth of microbes with a modified cellulose fiber |
| WO2012091965A1 (en) | 2010-12-17 | 2012-07-05 | Carnegie Mellon University | Electrochemically mediated atom transfer radical polymerization |
| MX353539B (es) | 2011-05-23 | 2018-01-17 | Gp Cellulose Gmbh Star | Fibra kraft de madera blanda que tiene blancura y brillo mejorados, y metodos para preparala y usarla. |
| AU2012276247B2 (en) * | 2011-06-30 | 2017-06-29 | Nano-Green Biorefineries Inc. | Catalytic biomass conversion |
| EP2747753B1 (de) | 2011-08-22 | 2023-03-29 | Carnegie Mellon University | Radikalische atomtransfer-polymerisation unter biologisch verträglichen bedingungen |
| CN104302831A (zh) | 2012-01-12 | 2015-01-21 | Gp纤维素股份有限公司 | 具有降低的黄变特性的低粘性牛皮纸纤维及其制造和使用方法 |
| WO2013123513A1 (en) * | 2012-02-17 | 2013-08-22 | PHARMA, Thinq | Use of metalloporphyrins and salen complexes for the catalytic oxidation of organic compounds |
| US9533297B2 (en) | 2012-02-23 | 2017-01-03 | Carnegie Mellon University | Ligands designed to provide highly active catalyst complexes |
| US8871051B2 (en) * | 2012-03-21 | 2014-10-28 | Los Alamos National Security, Llc | Process for decomposing lignin in biomass |
| CN106968127B (zh) | 2012-04-18 | 2019-03-01 | Gp纤维素股份有限公司 | 用于粘胶溶液的针叶木牛皮纸浆 |
| JP6472758B2 (ja) | 2013-02-08 | 2019-02-20 | ゲーペー ツェルローゼ ゲーエムベーハー | 改善されたα−セルロース含量を有する軟材クラフト繊維およびその化学セルロース製品の生産における使用 |
| BR112015019882A2 (pt) | 2013-03-14 | 2017-07-18 | Gp Cellulose Gmbh | fibra kraft clareada oxidada e métodos para fazer polpa kraft e fibra kraft de madeira macia e para clarear polpa kraft de celulose em sequência de branqueamento de multi-estágios |
| BR112015020000A2 (pt) | 2013-03-15 | 2017-07-18 | Gp Cellulose Gmbh | fibra kraft quimicamente modificada e métodos de fabricação da mesma |
| US9982070B2 (en) | 2015-01-12 | 2018-05-29 | Carnegie Mellon University | Aqueous ATRP in the presence of an activator regenerator |
| AR104940A1 (es) * | 2015-06-10 | 2017-08-23 | Chemsenti Ltd | Método para generar dióxido de cloro |
| AR104939A1 (es) * | 2015-06-10 | 2017-08-23 | Chemsenti Ltd | Método oxidativo para generar dióxido de cloro |
| EA201891627A1 (ru) | 2016-01-28 | 2019-03-29 | Нано-Грин Байорифайнериз Инк. | Получение кристаллической целлюлозы |
| EP3541849B1 (de) | 2016-11-16 | 2023-11-15 | GP Cellulose GmbH | Modifizierte cellulose aus chemischen fasern und methoden zu deren herstellung und verwendung |
| US11174325B2 (en) | 2017-01-12 | 2021-11-16 | Carnegie Mellon University | Surfactant assisted formation of a catalyst complex for emulsion atom transfer radical polymerization processes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0458397B1 (de) * | 1990-05-21 | 1997-03-26 | Unilever N.V. | Bleichmittelaktivierung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2633925B1 (fr) * | 1988-07-06 | 1990-10-26 | Elf Aquitaine | Procede d'oxydation par catalyse biomimetique d'alcools benzyliques et de composes apparentes |
| SE466061B (sv) * | 1990-04-23 | 1991-12-09 | Eka Nobel Ab | Blekning av kemisk massa genom behandling med foerst ett komplexbildande aemne och sedan ett peroxidinnehaallande aemne |
| US5153161A (en) * | 1991-11-26 | 1992-10-06 | Lever Brothers Company, Division Of Conopco, Inc. | Synthesis of manganese oxidation catalyst |
-
1992
- 1992-06-22 FR FR9207577A patent/FR2692499B1/fr not_active Expired - Fee Related
-
1993
- 1993-06-21 CA CA002138797A patent/CA2138797A1/fr not_active Abandoned
- 1993-06-21 US US08/356,283 patent/US5630906A/en not_active Expired - Fee Related
- 1993-06-21 DE DE69313284T patent/DE69313284D1/de not_active Expired - Lifetime
- 1993-06-21 NZ NZ253184A patent/NZ253184A/en unknown
- 1993-06-21 EP EP93913166A patent/EP0647158B1/de not_active Expired - Lifetime
- 1993-06-21 WO PCT/FR1993/000613 patent/WO1994000234A1/fr active IP Right Grant
- 1993-06-21 JP JP6502092A patent/JPH08500856A/ja active Pending
- 1993-06-21 AU AU43333/93A patent/AU671284B2/en not_active Ceased
- 1993-06-21 BR BR9306591A patent/BR9306591A/pt not_active Application Discontinuation
- 1993-06-21 AT AT93913166T patent/ATE157024T1/de not_active IP Right Cessation
-
1994
- 1994-12-21 FI FI945990A patent/FI945990A/fi not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0458397B1 (de) * | 1990-05-21 | 1997-03-26 | Unilever N.V. | Bleichmittelaktivierung |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4333393A (en) | 1994-01-24 |
| EP0647158B1 (de) | 1997-08-20 |
| CA2138797A1 (fr) | 1994-01-06 |
| FI945990A (fi) | 1995-02-21 |
| BR9306591A (pt) | 1998-12-08 |
| JPH08500856A (ja) | 1996-01-30 |
| US5630906A (en) | 1997-05-20 |
| FR2692499A1 (fr) | 1993-12-24 |
| NZ253184A (en) | 1995-09-26 |
| FI945990A0 (fi) | 1994-12-21 |
| DE69313284D1 (de) | 1997-09-25 |
| EP0647158A1 (de) | 1995-04-12 |
| FR2692499B1 (fr) | 1994-08-26 |
| ATE157024T1 (de) | 1997-09-15 |
| WO1994000234A1 (fr) | 1994-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |